Thienamycin

ChemicalBook > CAS DataBase List > Thienamycin

Product Name: Thienamycin
CAS No.: 59995-64-1
Chemical Name: Thienamycin
Synonyms: Imipenem EP Impurity A;(+)-Thienamycin;Thienamycin (>80%);IMipeneM IMpurity A;Thienamycin USP/EP/BP;Imipenemum Impurity A;(3As,7As)-Octahydro-2-benzofuran;Imipenem Impurity 1(Imipenem EP Impurity A);(5R)-3-(2-Aminoethylthio)-6β-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid;(5R)-3-[(2-Aminoethyl)thio]-6β-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CBNumber: CB8969644
Molecular Formula: C11H16N2O4S
Formula Weight: 272.32
MOL File: 59995-64-1.mol

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Thienamycin Property

alpha: D27 +82.7° (c = 1.0 in water)
Boiling point:: 514.0±50.0 °C(Predicted)
Density: 1.50±0.1 g/cm3(Predicted)
storage temp.: Hygroscopic, -86°C Freezer, Under inert atmosphere
solubility: Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
form: Solid
pka: 4.20±0.40(Predicted)
color: Off-White to Dark Yellow
Stability:: Hygroscopic, Temperature Sensitive, Very Unstable
InChI: InChI=1S/C11H16N2O4S/c1-5(14)8-6-4-7(18-3-2-12)9(11(16)17)13(6)10(8)15/h5-6,8,14H,2-4,12H2,1H3,(H,16,17)/t5-,6-,8-/m1/s1
InChIKey: WKDDRNSBRWANNC-ATRFCDNQSA-N
SMILES: N12[C@@]([H])([C@@H]([C@H](O)C)C1=O)CC(SCCN)=C2C(O)=O

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC

Product number: T344270
Product name: Thienamycin(>80%)
Packaging: 1mg
Price: $245
Updated: 2021/12/16

TRC

Product number: T344270
Product name: Thienamycin(>80%)
Packaging: 10mg
Price: $1940
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: API0010098
Product name: THIENAMYCIN
Purity: 80.00%
Packaging: 1MG
Price: $1504.68
Updated: 2021/12/16

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Thienamycin Chemical Properties,Usage,Production

Description

Thienamycin, one of the most potent naturally-produced antibiotics known thus far, was discovered in Streptomyces cattleya in 1976. Thienamycin has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes.

Uses

Thienamycin is one of the most potent naturally produced antibiotics known thus far. It has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes.

Definition

ChEBI: Thienamycin is a member of carbapenems.

Biosynthesis

The formation of thienamycin is thought to occur through a different pathway from classic β-lactams (penicillins, cephalosporins). Production of classic β-lactams in both fungi and bacteria occur through two steps: First, the condensation of L-cysteine, L-Valine, and L-α-amino adipic acid by ACV synthetase (ACVS, a nonribsomal peptide synthetase) and then cyclization of this formed tripeptide by isopenicillin N synthetase (IPNS).

Mechanism of action

In vitro, thienamycin employs a similar mode of action as penicillins through disrupting the cell wall synthesis (peptidoglycan biosynthesis) of various Gram-positive and Gram-negative bacteria (Staphylococcus aureus,Staphylococcus epidermidis, Pseudomonas aeruginosa to name a few). In a study carried out by Spratt et al., they found that, although thienamycin binds to all of the penicillin-binding proteins (PBP) in Escherichia coli, it preferentially binds to PBP-1 and PBP-2, which are both associated with the elongation of the cell wall. Unlike pencillins, which are rendered ineffective through rapid hydrolysis by the β-lactamase enzyme present in some strains of bacteria, thienamycin remains antimicrobially active. Neu et al. found that thienamycin displayed high activity against bacteria that were resistant to other β-lactamase stable compounds (cephalosporins), highlighting the superiority of thienamycin as an antibiotic among β-lactams.

Clinical Use

Thienamycin itself is extremely unstable and decomposes in aqueous solution. Consequently, thienamycin is impractical for clinical treatment of bacterial infections. For this reason, stable derivatives of thienamycin were created for medicinal consumption. One such derivative, imipenem, was formulated in 1985. Imipenem, an N-formimidoyl derivative of thienamycin, is rapidly metabolized by the renal dihydropeptidase enzyme found in the human body. To prevent its rapid degradation, imipenem is normally co-administered with cilastatin, an inhibitor of this enzyme.

Thienamycin Preparation Products And Raw materials

Raw materials

Autolyzed yeast Phosphate Buffer solution Nitrogen D(+)-Glucose Polyethylene Glycol

Preparation Products

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View Lastest Price from Thienamycin manufacturers

Dideu Industries Group Limited

Product: Thienamycin 59995-64-1
Price: US $1.10/g
Min. Order: 1g
Purity: 99.9%
Supply Ability: 100 Tons Min
Release date: 2021-06-21

Career Henan Chemical Co

Product: Thienamycin 59995-64-1
Price: US $1.00/g
Min. Order: 1g
Purity: ≥98%
Supply Ability: g/kg/Ton
Release date: 2019-12-25

59995-64-1, ThienamycinRelated Search:

IMipeneM-d4 Imipenem Impurity Imipenem Impurity Imipenem EP Impurity B Imipenem Impurity 4 Imipenem TRANS-2-HEPTENE Meropenem Trihydrate p-Nitrobenzyl (5R,6S)-2-(diphenylphosphoryloxy)-6-((1R)-1-hydroxyethyl)carbapen-2-em-3-carboxylate Ertapenem sodium Protected Imipenem Thienamycin Ertapenem Imipenem Doripenem Doripenem hydrate Biapenem Protected meropenem

[SR-[5α，6α(R^<*>^)]]-3-[(2-Aminoethyl)thio]-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

(5R)-3-(2-Aminoethylthio)-6β-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid

(5R)-3-[(2-Aminoethyl)thio]-6β-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

(5R,6R)-3-(2-aminoethylsulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

(5R,6R)-3-(2-aminoethylthio)-6-[(1R)-1-hydroxyethyl]-7-keto-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

(5R,6R)-3-(2-azanylethylsulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

IMipeneM IMpurity A

Imipenem EP Impurity A

Imipenem Impurity 1(Imipenem EP Impurity A)

(5R,6S)-3-(2-aminoethylthio)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[(2-aminoethyl)thio]-6-[(1R)-1-hydroxyethyl]-7-oxo-, (5R,6S)-

(3As,7As)-Octahydro-2-benzofuran

Thienamycin USP/EP/BP

Thienamycin (>80%)

(+)-Thienamycin

Imipenemum Impurity A

59995-64-1